Regioselective ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp3)-H bonds: efficient construction of 2,3-dihydropyrimidinesulfonamides |
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| Authors: | Wang Yang Chi Yue Zhang Wen-Xiong Xi Zhenfeng |
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| Affiliation: | Beijing National Laboratory for Molecular Sciences, and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemisstry, Peking University, Beijing 100871, China. |
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| Abstract: | A highly regioselective base-mediated ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp(3))-H bonds is achieved for the first time to afford efficiently 2,3-dihydropyrimidinesulfonamides. The mechanism of the ring expansion via tandem 4π electrocyclic ring-opening/1,5-H shift/6π electrocyclic ring-closing is well confirmed by the trapping experiments of two key intermediates and deuterium labeling studies. |
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